Winter Haven Homes with Gated Amenities

Winter Haven Homes with Gated Amenities

Welcome to Winter Haven, Florida, a charming city nestled in the heart of Polk County, renowned for its picturesque lakes and vibrant community spirit. With its stunning natural beauty and a wealth of recreational opportunities, Winter Haven is an ideal destination for families, retirees, and anyone looking to embrace a lifestyle that balances tranquility with adventure.

As you explore the real estate options in Winter Haven, you'll discover a variety of homes that offer gated amenities, providing an added layer of security and exclusivity. These gated communities are designed to cater to those who value privacy and peace of mind, while still being part of a welcoming neighborhood. Imagine coming home to a beautifully landscaped enclave, where access is limited to residents and their guests, allowing you to enjoy your surroundings in a safe and serene environment.

Many of these gated homes feature luxurious amenities such as resort-style pools, fitness centers, and meticulously maintained common areas, fostering a sense of community among residents. Whether you’re looking for a cozy single-family home or a spacious villa, Winter Haven's gated communities offer a range of options to suit your lifestyle.

Beyond the gates, Winter Haven boasts an array of attractions, from the famous Legoland Florida Resort to the serene waters of the Chain of Lakes, perfect for boating, fishing, and leisurely strolls. With its warm climate and friendly atmosphere, Winter Haven is not just a place to live; it’s a place to thrive. Come discover your dream home in this enchanting city where every day feels like a vacation!

Newest Winter Haven Homes with Gated Amenities

$249,900
2 Beds ⋅ 2 Baths ⋅ Cypresswood SubDv. ⋅ 33884 Zip Code
BEAUTIFUL VILLA READY TO MOVE IN! A brand-new HVAC system (June 2026), along with new insulation throughout the attic. Features include cathedral ceilings, elegant detailed baseboard trim with decorative corner blocks throughout, new flooring, plantation shutters on the windows, and three sets of French doors. The upgraded kitchen features stainless steel appliances, double ovens, and a built-in pantry with pull-out shelves. A utility closet provides additional storage, and the interior laundry room includes a full-size washer and dryer. The primary bathroom features dual showers and two vanities with wood cabinetry, while the second bathroom includes a jetted bathtub and wood cabinet vanity. Golf course frontage and two outdoor patio areas, with one overlooking the 8th fairway, plus a second patio with concrete privacy walls. Cypresswood Country Club community offers golf, a Jr. Olympic-size pool, tennis courts, a restaurant and bar, social events, live music three nights a week, and lush, well-maintained surroundings. Come take a look at this one!

2801 Wingfoot Court, Winter Haven
$289,000
3 Beds ⋅ 2 Baths ⋅ Gardens Ph 01 SubDv. ⋅ 33880 Zip Code
Welcome home to this beautifully refreshed 3-bedroom, 2-bathroom home offering a comfortable layout, fresh updates, and an expansive backyard with plenty of possibilities. Step inside to discover all-new flooring and fresh interior paint, creating a bright, clean, and inviting atmosphere throughout the home. The spacious living areas provide a versatile setting for both everyday living and entertaining, with plenty of natural light adding to the welcoming feel. The well-designed floor plan offers three comfortable bedrooms and two full bathrooms, providing plenty of space for a variety of needs. The attached two-car garage adds valuable parking, storage, and everyday convenience. Outside, the sprawling backyard is one of the home's standout features, offering abundant space to entertain, garden, enjoy outdoor activities, or create your own private retreat. Whether you envision a large outdoor gathering area, garden space, play area, or simply room to relax and enjoy the outdoors, the possibilities are plentiful. With fresh interior updates, a functional layout, generous living space, an attached two-car garage, and an expansive backyard, this home is ready for its next chapter. Come see all that this refreshed home has to offer and schedule your showing today!

212 Majestic Gardens Lane, Winter Haven
$549,999
3 Beds ⋅ 3 Baths ⋅ Lake Ashton West Ph Ii North SubDv. ⋅ 33884 Zip Code
*GOLF COURSE and WATER VIEWS*** Located behind the secure gates of the coveted 55 + community of Lake Ashton, the views from the covered and screened lanai are superb! Built in 2019, this home offers TWO SUITES, ONE GUEST BEDROOM and THREE BATHS. This split floor plan home offers great curb appeal with a FRESH NEW EXTERIOR COAT OF PAINT, Paver Driveway and Well Maintained Landscape. The lawn is "watered" by an irrigation system. As you enter thru the double glass doors of this home you are greeted by a large open floor plan offering expansive views of the golf course and lake beyond. The views from this coveted lot location are spectacular so make sure you bring your binoculars! The living room, formal dining area and kitchen flow seamlessly together in this modified ASHTON Floor plan home, making entertaining easy and fun! The spacious Living Room has a tray ceiling, floor outlets, ceiling fan and triple sliders that stack and open to the covered and screened lanai. A formal dining area is located to the left of the front entry and the arched double windows add a touch of class! The Kitchen features 42" wood cabinetry, breakfast bar, pendant lighting, granite countertops, SS appliances (microwave replaced Sept. 2026) and ample counter top space for food prep and food display. The Dinette area is conveniently located off of the kitchen and the double windows provide an abundance of natural light into the home. Double sliders provide access to the lanai from the dinette area. The spacious and oversized Primary Suite with double door entry makes up the right wing of the home. It showcases two large walk-in closets, a separate water closet with window, a linen closet, a large, tiled walk in shower with grab bars and a tiled bench to sit on. The vanity with double sinks compliments the bathroom area. The Primary Suite with trey ceiling and ceiling fans can accommodate a separate sitting area for relaxation or larger bedroom furniture. The 2nd Suite with double door entry is on the left side of the home. It's accessible from the dinette area and from the hallway that leads to the 3rd Bedroom/3 Bath. The 2nd Suite has a private bath and built in closet. The 2nd Suite Bath features a comfort height vanity, walk in shower with glass enclosure, grab bars, foot rest and comfort height toilet. Overnight Guests will enjoy their own bedroom and bath with shower/tub combo and comfort height vanity. The Laundry Room (FLEX ROOM) is spacious and well designed with a wash tub and portable storage units for your personal items. The washer/dryer are included in the sale of this home. The outdoor living space offers a delightful place for entertaining. There are two OPTIONS: You can enjoy the covered portion of the lanai or the extended/uncovered screened lanai with direct views of the golf course and lake. The double car garage is sizeable and there is a separate golf cart entrance. The home also has a WHOLE HOUSE GENERAC- this is a huge bonus! ADDITIONAL IMPROVEMENTS to this home include: NEW INTERIOR PAINT and NEW LUXURY VINYL FLOORING. The community of Lake Ashton is a hidden treasure with an aura of peace and tranquility, and offers 2 golf courses, tennis courts, 2 pools (one indoor and one outdoor) movie theater, bowling lanes, card, craft and billiard rooms, fitness centers, pickleball courts, indoor basketball, indoor racquetball, numerous recreational activities, and restaurants. Make an appointment today to TOUR THIS HOME!

6136 Pebble Beach Boulevard, Winter Haven
$106,000
2 Beds ⋅ 2 Baths ⋅ Lakeridge Condo SubDv. ⋅ 33881 Zip Code
**THIS CONDO IS PRICE TO SELL !!**CENTRAL FLORIDA 55+ Age GATED CONDOMINIUM COMPLEX WITH LAKE AND CITY VIEW. All new insulated windows throughout. This condominium provides 1,347 sq. ft. of living area & is located in the beautiful "Chain Of Lakes" City of Winter Haven, Fl. Very friendly complex w/ social activities offered if you wish to participate. Monthly association fee includes water, sewer, trash, fiber optic cable & internet, condo reserves, manager and use of recreational facilities. Lakeridge Condominiums offers a maintenance-free lifestyle w/ heated pool, tennis, shuffleboard, community room, gated entrances & covered assigned parking space. The large bright kitchen has plenty of cabinets & great counter space, appliances (dishwasher does not work) & pantry closet. The kitchen overlooks the 26'x14' great room that also adjoins the additional bonus space & storage closet. The 16X14 foot Primary bedroom suite has a walk in closet & bathroom w/ walk-in shower. Beautiful views of Spring Lake can be enjoyed from Primary bedroom & living areas. The 2nd bedroom & bath can be a private guest area or for your personal use for office, hobbies etc. The washer & dryer are included in the sale. Central heat and air conditioning. Convenient proximity to shopping, places of worship, groceries & restaurants. Extra assigned storage bin on same floor. Make this your full time home, winter home or investment property to update. Lakeridge Condominiums is an age-restricted, well-maintained & well-managed community. Sharepoint car charger provided for those with electric cars. Non-smoking property. 1 pet, 20 pounds or under may be approved.

1776 6th Street Nw Unit 304, Winter Haven
$370,000
4 Beds ⋅ 3 Baths ⋅ Overlook Estates East SubDv. ⋅ 33884 Zip Code
HOME SWEET HOME! This sweet 4 bedroom 3 bath home is ready for its next happy homeowner. Located in a small gated community in SE Winter Haven this one has the perfect combination of location, and comfort. Check out the homey kitchen with granite countertops and wood cabinets. The corner pantry can hold all your treats for those football weekend get togethers. The rooms have large windows offering abundant natural light, and space for everyone. The ideal 3 way split bedroom plan offers form, and function. The spacious yard offers peace, and privacy with a PVC-fenced back yard, and extra storage in a charming 10x12 planters shed. The 2025 architectural shingle roof, 2017 AC dual zone AC system, and Generac generator have you covered in all Florida weather. Check out this sweet property today. Step inside, fall in love. Make it yours!

754 Santa Maria Dr, Winter Haven
$199,900
Village Spirit Lake Ph 01 SubDv. ⋅ 33880 Zip Code
LAST BUILDING LOT ON SPIRIT LAKE IN THE VILLAGES OF SPIRIT LAKE, SO BRING YOUR PLANS AND START ENJOYING THIS GATED COMMUNITY. OFFERING A PRIVATE BOAT LAUNCH, FISHING DOCK PLUS COMMUNITY POOL, CLUBHOUSE, PLAY GROUND, TENNIS, BASKETBALL AND PICKLEBOARD COURTS. EAST ACCESS TO THE POLK PARKWAY SO COMMUTES TO TAMPA OR ORLANDO MAKE IT EASY. OWNER TERMS AVAILABLE IF NEEDED WHILTE GETTING YOUR CONSTRUCTION PLANS TOGETHER.

Archaic Drive, Winter Haven
$699,000
4 Beds ⋅ 3 Baths ⋅ Hart Lake Hills Ph 01 SubDv. ⋅ 33884 Zip Code
From the moment you enter, it is immediately apparent this is not your typical lakefront home. Elevated sightlines extend across the pool to the tranquil waters of Hart Lake, creating a dramatic first impression and an almost infinity-edge style of living. Situated on approximately half an acre in the gated SE Winter Haven community of Hart Lake Hills, this immaculate custom residence offers 4 bedrooms, 3 baths and over 2,500 SF of refined living space with a level of finish and customization rarely found at this price point. Designed for upscale everyday living and impressive entertaining, the home showcases gorgeous travertine and wood flooring, substantial millwork, designer lighting, custom tile and stonework, granite surfaces and distinctive architectural details throughout. Statement fixtures incorporating sculptural, crystal and glass elements add another layer of sophistication. The open, triple-split bedroom floor plan includes a spacious family room, formal dining, office/den, kitchen with dinette and inside laundry. The family room captures panoramic lake views through expansive glass doors opening to the pool and features a custom wood TV wall accented with natural-edge detailing. The kitchen offers quartz countertops, stainless appliances, custom wood cabinetry, breakfast bar and a light-filled dinette overlooking the pool and lake. The adjoining dining room is illuminated by a dramatic faceted glass chandelier, while the office/den room provides flexibility as an office, study or additional sitting room. The primary suite features wood flooring, a large walk-in closet with built-ins and an extraordinary spa-inspired bath. Travertine and stone surround a floating-edge soaking tub with black stone deck, dramatic underlighting and sleek linear fireplace. An oversized open shower features multiple body sprays, handheld fixture and rainfall shower, complemented by floating cabinetry, granite-topped vanity, designer lighting and a private water closet. Three generously sized guest bedrooms are privately positioned away from the primary suite with excellent closet space and access to beautifully customized guest baths. The third bath also serves the pool and features a glass-enclosed MrSteam steam shower. Outside, wide steps transition from the elevated interior to an expansive screened outdoor living area where the saltwater pool appears visually connected to Hart Lake beyond. A large covered lanai with travertine flooring offers room for dining and lounging, while generous deck space provides plenty of room for entertaining and enjoying the Florida sunshine. Hart Lake offers opportunities for fishing, boating and enjoying the natural waterfront setting. Additional features include double-pane windows, insulated sliding doors, central vacuum, irrigation well, 2019 roof, 2020 A/C and a pool enclosure refurbished in 2024 with new screening, doors and screws. All this and centrally located between Tampa and Orlando, approximately 10 minutes from shopping, dining and medical facilities, and within walking distance of Chain of Lakes Elementary.

644 Hart Lake Drive, Winter Haven
$425,000
4 Beds ⋅ 3 Baths ⋅ Lake Mariam Hills Rep SubDv. ⋅ 33884 Zip Code
Welcome home to this beautifully maintained four-bedroom, 2½-bathroom home located in a desirable gated community. New Roof installed along with a private access boat launch to Lake Mariam, perfect for enjoying Florida’s outdoor lifestyle. From the moment you walk through the front door, the home’s thoughtfully designed open floor plan immediately stands out. Your view leads straight through to the sparkling pool, creating a wonderful sense of space and bringing the outdoors in. The dining room is conveniently located to the right, while the spacious living room provides plenty of room for relaxing and entertaining. The kitchen features a large island with a breakfast bar, making it the perfect gathering spot for family and friends. Its open design allows you to prepare meals or wash dishes while still keeping an eye on the family enjoying the pool. Step outside to the expansive pool area, where there is plenty of space for outdoor dining, morning coffee, entertaining, or simply relaxing by the pool. It’s an ideal setting for enjoying the Florida sunshine year-round. The oversized master suite offers plenty of room to unwind and features a spacious master bathroom with a garden tub and dual vanity sinks. And there are some important recent updates to appreciate, including a new roof installed just one year ago and a new garage door. With its spacious floor plan, private lake access, boat launch, pool, oversized master suite, and recent improvements, this home offers the perfect combination of comfort, convenience, and Florida living—all within a gated community.

120 Lake Mariam Way, Winter Haven
$134,990
1 Beds ⋅ 1 Baths ⋅ Fairview Village SubDv. ⋅ 33881 Zip Code
Welcome Home to Easy Florida Living! Come discover this beautifully maintained 2023 Skyline Park Model, installed in August 2022 and thoughtfully designed with comfort, convenience, and relaxation in mind. From the moment you arrive, you’ll appreciate the new concrete driveway, newer roof, central air, spacious storage, and inviting outdoor living opportunities. Inside, the home offers an open and comfortable layout with a large pantry, dining island, electric fireplace, walk-in shower, and a bedroom spacious enough for a king-size bed. The home is being offered with many furnishings and features, including a French-door refrigerator, electric range, microwave, washer/dryer combo, water softener, blinds, generator ready and more. The lifestyle is just as appealing! The 99-year perpetual lease is renewable for only $1, while the current $90 monthly association fee includes water, sewer, trash, seasonal lawn maintenance, heated pool access, clubhouse, and a variety of community activities. Enjoy shuffleboard, horseshoes, billiards, ping pong, and a community dock with direct canal access to Lake Henry, complete with a pier bench and fire pit. Whether you’re looking for a seasonal retreat, a comfortable Florida getaway, or a place to enjoy the relaxed community lifestyle, this one is ready for you to come see and fall in love with it! Financing Available!

7060 Fairview Village Circle, Winter Haven
$115,000
2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv. ⋅ 33880 Zip Code
OVER $19,000 IN RECENT UPGRADES MEANS THE BIG-TICKET WORK HAS ALREADY BEEN DONE! This fully furnished Oakwood Estates home features a new roof (2023), plus new HVAC, electric water heater, rain gutters, and exterior porch tile (2024). Step inside to a bright, welcoming interior filled with natural light from double-pane windows. Luxury vinyl plank flooring flows throughout. The kitchen features stainless steel appliances, white cabinetry, wood-look countertops, and a newer sink. Built-in cabinetry adds charm and storage to the dining area, which opens to a spacious living room. Both bedrooms are generously sized, with a walk-in closet in the primary. A separate laundry room includes the washer and dryer. Enjoy additional living space in the Florida room and enclosed lanai, perfect for relaxing and enjoying the Florida lifestyle. Hurricane shutters, vinyl siding, and an updated electrical panel add even more value. Oakwood Estates is a gated, resident-owned 55+ community with two heated pools, two clubhouses, pickleball and tennis courts, shuffleboard, bocce ball, miniature golf, a fishing lake and pier, RV and boat storage, library, activities center, and an active social calendar. Major updates done, furnishings included, and ready for you to move in and enjoy!

4332 Cherrywood Street, Winter Haven
$165,900
2 Beds ⋅ 2 Baths ⋅ Eagle Pond Condo SubDv. ⋅ 33884 Zip Code
Looking for a COUNTRY CLUB LIFESTYLE? Conveniently located in Cypresswood Golf & Country Club, on Dundee Rd near HWY 27. RECENT UPDATES INCLUDE a 2 year old AC unit, and in 2026 brand New hot water heater, countertops throughout, dishwasher, microwave, disposal and kitchen faucet. This SUPER CLEAN 2 bed/2 bath condominium offers an open concept with 10' Ceilings, Crown Molding, 2" Blinds and Ceiling Fans throughout. You will love the spacious kitchen with pantry & lots of counter space. Both bedrooms feature walk in closets. Ample amount of closet space plus an outside storage room & assigned parking. Cypresswood residents enjoy a resort and country club lifestyle! The 18 hole golf course and Clubhouse with chef prepared meals & live music are open to the public. Additional amenities include Brand New tennis & pickleball courts, plus a half Olympic size pool. Located just minutes from trendy downtown Winter Haven, convenient to Hwy 27 & I-4. Close to Legoland, Bok Tower, shopping, dining, hospital and medical facilities. Just 5 minutes to BRAND NEW Publix and ALDI grocery's, 7-11 gas station & McDonalds.

508 Eagle Pond Drive Unit 508, Winter Haven
$200,000
2 Beds ⋅ 2 Baths ⋅ Vienna Square Ph 01 SubDv. ⋅ 33884 Zip Code
Short Sale. CLOSE IN 60 DAYS OR LESS! QUICK and easy HECM Short Sale on this 2 bedroom 2 bath Vienna Square home. This one can be a real charmer with your personal touches. Bright, light, and open floor plan. Sold strictly AS-IS. No renting for the 1st 2 years of ownership in this charming 55+ community. This home is conveniently located within 10 minutes of restaurants, banks, shopping and Legoland. Vienna Square offers a low-maintenance lifestyle with reasonable fees, in a welcoming setting. Vienna Square is a beautifully maintained, amenity-rich community designed for easy living. Monthly fees include exterior paint, roof replacement, irrigation water, basic yard maintenance, and a Spectrum Internet/TV package. Residents enjoy access to a community pool, fitness center, billiards, movie nights, tennis and pickleball courts, and an active social calendar. Step inside, fall in love. Make it yours!

2338 Salzburg Loop, Winter Haven
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